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Benzyl chloride, also known as alpha-chlorotoluene or phenylmethyl chloride, is an organic compound with the formula C6H5CH2Cl. It is a colorless liquid with a pungent odor. Benzyl chloride is an important industrial chemical used in the synthesis of many other organic compounds. It is a derivative of toluene where one of the methyl group's hydrogen atoms has been replaced by a chlorine atom.

The primary industrial method for producing benzyl chloride involves the free-radical chlorination of toluene. This reaction is typically carried out using chlorine gas under ultraviolet light or with radical initiators. The process needs careful control to minimize the formation of over-chlorinated products such as benzal chloride and benzotrichloride.

Benzyl chloride is highly reactive due to the presence of the benzylic halide functional group. It readily undergoes nucleophilic substitution reactions. This reactivity makes it a valuable intermediate in the production of benzyl alcohol, benzyl esters, and benzyl ethers. It is also used in the manufacture of pharmaceuticals, dyes, perfumes, and as a lachrymator (tear-producing agent).

Due to its irritating and corrosive properties, benzyl chloride requires careful handling. It is a lachrymator and skin irritant. Inhalation of vapors can cause respiratory distress. Proper safety precautions, including adequate ventilation and personal protective equipment, are essential when working with this chemical. Its environmental impact is also a consideration, as it is toxic to aquatic life and can persist in the environment.